The meeting with Masayoshi Son of SoftBank, initially scheduled for 90 minutes, was cut down to a brief 12 minutes in the office, culminating in a 16-minute car ride where the deal was discussed.
Neumann had originally planned to raise a modest $300 to $400 million for WeWork, a figure that was dramatically dwarfed by Son's proposal.
Masayoshi Son unexpectedly offered to invest $3 billion, a figure that quickly escalated to $4.2 Billion to cover WeWork's global entities, including operations in China, Japan, and Southeast Asia.
The significant investment deal was sealed informally with handwritten signatures on an iPad within the vehicle, marking a pivotal moment in WeWork's trajectory.
Neumann emphasizes the importance of pausing to reflect on 'why' and one's true intentions when faced with such large, unsolicited offers, noting that while he doesn't blame the investor, accepting such a substantial sum profoundly impacted the business.